Compound containing a 5-membered heterocycle and organic light-emitting diode using same, and terminal for same

ABSTRACT

Disclosed are a novel-structural compound including a 5-membered heterocycle, an organic electronic device using the same, and a terminal thereof.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to a compound containing a 5-memberedheterocycle, an organic electronic device using the same, and a terminalthereof.

2. Description of the Prior Art

In general, an organic light emitting phenomenon indicates conversion ofelectric energy into light energy by means of an organic material. Anorganic electronic device using the organic light emitting phenomenongenerally has a structure including an anode, a cathode, and an organicmaterial layer interposed therebetween. Herein, in many cases, theorganic material layer may have a multi-layered structure havingrespective different materials in order to improve efficiency andstability of an organic electronic device. For example, it may include ahole injection layer, a hole transport layer, a light emitting layer, anelectron transport layer, an electron injection layer, and the like.

Materials used as an organic material layer in an organic electronicdevice may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, etc. according to their functions. Then, the lightemitting material may be divided into a high molecular weight type and alow molecular weight type according to their molecular weight, and maybe divided into a fluorescent material from electronic singlet excitedstates and a phosphorescent material from electronic triplet excitedstates according to their light emitting mechanism. Further, the lightemitting material can be classified into a blue, green or red lightemitting material and a yellow or orange light emitting materialrequired for giving a more natural color, according to a light emittingcolor.

Meanwhile, when only one material is used as a light emitting material,an efficiency of a device is lowered owing to a maximum luminescencewavelength being moved to a longer wavelength due to the interactionbetween the molecules, the deterioration of color purity and thereduction in light emitting efficiency. Therefore, a host/dopant systemcan be used as the light emitting material for the purpose of enhancingthe color purity and the light emitting efficiency through energytransfer. It is based on the principle that if a small amount of adopant having a smaller energy band gap than a host forming a lightemitting layer is mixed with the light emitting layer, excitons whichare generated in the light emitting layer are transported to the dopant,thus emitting a light having a high efficiency. Here, since thewavelength of the host is moved according to the wavelength of thedopant, a light having a desired wavelength can be obtained accordingthe kind of the dopant.

In order to allow the organic electronic device to fully exhibit theabove-mentioned excellent characteristics, a material constituting theorganic material layer in the device, for example, a hole injectionmaterial, a hole transport material, a light emitting material, anelectron transport material and an electron injection material should beessentially composed of a stable and efficient material. However, thedevelopment of a stable and efficient organic material layer materialfor the organic electronic device has not yet been fully realized.Accordingly, the development of new materials is continuously desired.

SUMMARY OF THE INVENTION

An object of the present invention is to provide a novel-structuralcompound including a 5-membered heterocycle, an organic electronicdevice using the same, and a terminal thereof, in which high efficiency,color purity improvement, and long lifetime of the light emitting devicecan be achieved due to the characteristics of the compound.

In accordance with an aspect of the present invention, there is provideda compound represented by Formula below.

The inventive novel-structural compound including a 5-memberedheterocycle may be used as a hole injection material, a hole transportmaterial, a light emission material, and an electron transport materialappropriate for a fluorescent or phosphorescent device of all colors(such as red, green, blue, white, etc.) according to synthesizedcompounds in an organic electronic device, and is useful as a hostmaterial for various colors of a phosphorescent dopant.

Accordingly, the present invention provides a novel-structural compoundincluding a 5-membered heterocycle, an organic electronic device usingthe same, and a terminal thereof.

According to the present invention, the organic light emitting diodeusing the compound including a 5-membered heterocycle may be used as ahole injection material, a hole transport material, a light emissionmaterial, and an electron transport material appropriate for afluorescent or phosphorescent device of all colors, and is useful as ahost material for various colors of a phosphorescent dopant. Also, thecompound may be used as a fluorescent or phosphorescent host material ofa light emitting device, thereby significantly improving luminousefficiency, color purity, and lifetime.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other objects, features and advantages of the presentinvention will be more apparent from the following detailed descriptiontaken in conjunction with the accompanying drawings, in which:

FIGS. 1 to 6 show examples of an organic light emitting diode which canemploy a compound according to the present invention.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

Hereinafter, exemplary embodiments of the present invention will bedescribed in detail with reference to the accompanying drawings. Inreference numerals given to components of respective drawings, it shouldbe noticed that same components are designated by the same referencenumerals as far as possible although they are illustrated in differentdrawings. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component.

The present invention provides a compound represented by Formula 1below.

(1) R₁ through R₁₀ each are independently selected from the groupconsisting of a hydrogen atom, a halogen atom, a cyano group, an alkoxygroup, a thiol group, a substituted or unsubstituted alkyl group having1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having1 to 50 carbon atoms, a substituted or unsubstituted alkenyl grouphaving 1 to 50 carbon atoms, a substituted or unsubstituted arylenegroup having 5 to 60 carbon atoms, a substituted or unsubstituted arylgroup having 5 to 60 carbon atoms, a substituted or unsubstitutedaryloxy group having 5 to 60 carbon atoms, a substituted orunsubstituted C₁˜C₅₀ alkyl group having at least one of sulfur (S),nitrogen (N), oxygen (O), phosphorous (P) and silicon (Si), asubstituted or unsubstituted C₅˜C₆₀ heteroaryl group having at least oneof sulfur (S), nitrogen (N), oxygen (O), phosphorous (P) and silicon(Si), and a substituted or unsubstituted C₅˜C₆₀ heteroaryloxy grouphaving at least one of sulfur, nitrogen, oxygen, phosphorous andsilicon.

(2) R₁ through R₁₀ each may form a substituted or unsubstitutedsaturated or unsaturated ring together with an adjacent group.

(3) X is at least one selected from sulfur, oxygen or silicon.

(4) Y is selected from the group consisting of a hydrogen atom, ahalogen atom, a cyano group, an alkoxy group, a thiol group, asubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms, asubstituted or unsubstituted alkenyl group having 1 to 50 carbon atoms,a substituted or unsubstituted arylene group having 5 to 60 carbonatoms, a substituted or unsubstituted aryl group having 5 to 60 carbonatoms, a substituted or unsubstituted aryloxy group having 5 to 60carbon atoms, a substituted or unsubstituted C₁˜C₅₀ alkyl group havingat least one of sulfur, nitrogen, oxygen, phosphorous and silicon, asubstituted or unsubstituted C₅˜C₆₀ heteroaryl group having at least oneof sulfur, nitrogen, oxygen, phosphorous and silicon, and a substitutedor unsubstituted C₅˜C₆₀ heteroaryloxy group having at least one ofsulfur, nitrogen, oxygen, phosphorous and silicon.

(5) n is an integer from 1 to 3.

(6) the compound having the structural formula above may be used for asoluble process.

Formula 1 may be represented by Formulas 2 to 7 below according topreparation and synthesis methods.

Formula 2 above may be represented by Formula 8 below.

Formula 3 above may be represented by Formula 9 below.

Formula 4 above may be represented by Formula 10 below.

Formula 5 above may be represented by Formula 11 below.

Formula 6 above may be represented by Formula 12 below.

Formula 7 above may be represented by Formula 13 below.

According to one embodiment of the present invention, specific examplesof a compound including a 5-membered heterocycle, represented by Formula1 may include compounds represented by Formulas 2 to 7, and further maybe represented by Formulas 8 to 13. However, the present invention isnot limited thereto.

There exist various organic electronic devices which employ compoundsincluding a 5-membered heterocycle, as described with reference toFormulas 1 to 13, as an organic material layer. The organic electronicdevices in which compounds including a 5-membered heterocycle, asdescribed with reference to Formulas 1 to 13, can be employed, mayinclude, for example, an organic light emitting diode (OLED), an organicsolar cell, an organic photo conductor (OPC) drum, an organic transistor(organic TFT), and the like.

As one example of the organic electronic devices in which compoundsincluding a 5-membered heterocycle, as described with reference toFormulas 1 to 13, can be used, an organic light emitting diode (OLED)will be described below, but the present invention is not limitedthereto. The above described compound including a 5-membered heterocyclemay be applied to various organic electronic devices.

In another embodiment of the present invention, there is provided anOLED including a first electrode, a second electrode, and an organicmaterial layer interposed between these electrodes, in which at leastone of organic material layers includes the compounds represented byFormulas 1 to 13.

FIGS. 1 to 6 show examples of an OLED which can employ a compoundaccording to the present invention.

The OLED according to another embodiment of the present invention may bemanufactured by means of a manufacturing method and materialsconventionally known in the art in such a manner that it can have aconventionally known structure, except that at least one of organicmaterial layers including a hole injection layer, a hole transportlayer, a light emitting layer, an electron transport layer, and anelectron injection layer is formed in such a manner that it can includethe compounds represented by Formulas 1 to 13.

The structures of the OLED according to another embodiment of thepresent invention are shown in FIGS. 1 to 6, but the present inventionis not limited to the structures. Herein, in the embodiment shown inFIG. 1, the reference numeral 101 indicates a substrate, 102 indicatesan anode, 103 indicates a hole injection layer (HIL), 104 indicates ahole transport layer (HTL), 105 indicates a light emitting layer (EML),106 indicates an electron injection layer (EIL), 107 indicates anelectron transport layer (ETL), and 108 indicates a cathode. Althoughnot shown, such an OLED may further include a hole blocking layer (HBL)for blocking movement of holes, an electron blocking layer (EBL) forblocking movement of electrons, and a protective layer. The protectivelayer may be formed in such a manner that it, as an uppermost layer, canprotect an organic material layer or a cathode.

Herein, the compound including a 5-membered heterocycle, as describedwith reference to Formulas 1 to 13, may be included in at least one oforganic material layers including a hole injection layer, a holetransport layer, a light emitting layer, and an electron transportlayer. Specifically, the compound including a 5-membered heterocycle, asdescribed with reference to Formulas 1 to 13, may be substituted for atleast one of a hole injection layer, a hole transport layer, a lightemitting layer, an electron transport layer, an electron injectionlayer, a hole blocking layer, an electron blocking layer, and aprotective layer, or may be used in combination with these layers. Ofcourse, the compound may be used for not only one layer of the organicmaterial layers but also two or more layers.

Especially, the compound including a 5-membered heterocycle, asdescribed with reference to Formulas 1 to 13, may be used as a materialfor hole injection, hole transport, electron injection, electrontransport, light emission, and passivation (capping). Especially, it maybe used alone as a light emitting material, a host or a dopant.

For example, in manufacturing of the OLED according to anotherembodiment of the present invention, a metal, a conductive metal oxide,or an alloy thereof is deposited on a substrate by means of PVD(physical vapor deposition) such as sputtering or e-beam evaporation soas to form an anode, and then an organic material layer including a holeinjection layer, a hole transport layer, a light emitting layer, anelectron transport layer, and an electron injection layer is formedthereon, and a material used as a cathode is deposited thereon.

Besides, on a substrate, a cathode material, an organic material layer,and an anode material may be sequentially deposited so as to provide anorganic electronic device. The organic material layer may be formed in amulti-layered structure including a hole injection layer, a holetransport layer, a light emitting layer, an electron transport layer,and an electron injection layer, but the present invention is notlimited thereto. It may be formed in a single layer structure. Further,the organic material layer may be manufactured with a smaller number oflayers by using various polymer materials by means of a solvent process(e.g., spin coating, dip coating, doctor blading, screen printing,inkjet printing, or thermal transfer) instead of deposition.

In the OLED according to another embodiment of the present invention,the organic material layer may be formed by a soluble process, such as aspin coating process or an inkjet process, of the above describedcompound including a 5-membered heterocycle.

The substrate is a support for the OLED, and may employ a silicon wafer,a quartz or glass plate, a metallic plate, a plastic film or sheet.

On the substrate, an anode is positioned. Such an anode allows holes tobe injected into a hole injection layer positioned thereon. As an anodematerial, a material having a high work function is preferably used sothat injection of holes into an organic material layer can be smoothlycarried out. Specific examples of an anode material used for the presentinvention may include: metals (such as vanadium, chromium, copper, zinc,gold) or alloys thereof; metallic oxides such as zinc oxide, indiumoxide, indium tin oxide (ITO), indium zinc oxide (IZO); a metal-oxidecombination such as ZnO:Al or SnO₂:Sb; and conductive polymers such aspoly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT),polypyrrole and polyaniline, but the present invention is not limitedthereto.

On the anode, a hole injection layer is positioned. A material for sucha hole injection layer is required to have a high efficiency forinjecting holes from an anode, and to be able to efficiently transportthe injected holes. For this, the material has a low ionizationpotential, a high transparency against visible light, and a highstability for holes.

As a hole injection material, a material into which holes can be wellinjected from an anode at a low voltage is used. Preferably, HOMO(highest occupied molecular orbital) of the hole injection materialranges from a work function of an anode material to HOMO of adjacentorganic material layers. Specific examples of the hole injectionmaterial may include metal porphyrine-, oligothiophene-, andarylamine-based organic materials, hexanitrile hexaazatriphenylen- andquinacridone-based organic materials, perylene-based organic materials,and anthraquinone-, polyaniline-, and polythiophene-based conductivepolymers, but the present invention is not limited thereto.

On the hole injection layer, a hole transport layer is positioned. Sucha hole transport layer receives holes transferred from the holeinjection layer and transfers them to an organic luminescence layerpositioned thereon. Further, the hole transport layer has a high holemobility and a high hole stability and performs a role of blockingelectrons. Besides these general requirements, it requiresheat-resistance against a device when applied for car display, and thusis preferably made of a material having a glass transition temperature(Tg) of 70° C. or more. The examples of a material satisfying theseconditions may include NPD (or NPB), spiro-arylamine-based compound,perylene-arylamine-based compound, azacycloheptatriene compound,bis(diphenylvinylphenyl)anthracene, silicongermaniumoxide compound,silicon-based arylamine compound, and the like.

On the hole transport layer, an organic luminescence layer ispositioned. Such an organic luminescence layer is made of a materialhaving a high quantum efficiency, in which holes and electrons which areinjected from an anode and a cathode, respectively, are recombined so asto emit light. As a light emitting material, a material allowing holesand electrons transferred from a hole transport layer and an electrontransport layer, respectively, to be combined so as to emit visiblelight is used. Preferably, a material having a high quantum efficiencyagainst fluorescence or phosphorescence is used.

As a material or a compound satisfying these conditions, for a greencolor, Alq3 may be used, and for a blue color, Balq(8-hydroxyquinolineberyllium salt), DPVBi(4,4′-bis(2,2-diphenylethenyl)-1,1′-biphenyl)based, Spiro material,spiro-DPVBi(Spiro-4,4′-bis(2,2-diphenylethenyl)-1,1′-biphenyl),LiPBO(2-(2-benzoxazoyl)-phenol lithium salt),bis(diphenylvinylphenylvinyl)benzene, aluminum-quinoline metal complex,imidazole, thiazol and oxazole-metal complex, or the like may be used.In order to improve the luminous efficiency of a blue color, perylene,andBczVBi(3,3′[(1,1′-biphenyl)-4,4′-diyldi-2,1-ethenediyl]bis(9-ethyl)-9H-carbazole;DSA(distrylamine)) may be doped in a small amount. For a red color, agreen light emitting material may be doped withDCJTB([2-(1,1-dimethylethyl)-6-[2-(2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H-benzo(ij)quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene]-propanedinitrile)in a small amount. When a process such as inkjet printing, roll coating,spin coating, is used to form a light emitting layer,polyphenylenevinylene (PPV)-based polymer or poly fluorene may be usedfor an organic luminescence layer.

On the organic luminescence layer, an electron transport layer ispositioned. Such an electron transport layer requires a material whichhas a high efficiency for electrons injected from a cathode positionedthereon, and can efficiently transport the injected electrons. For this,a material having a high electron affinity, a high electron mobility,and a high electron stability is required. The examples of an electrontransport material satisfying these conditions may include Al complex of8-hydroxyquinoline; complex including Alq₃; organic radical compound;and hydroxyflavone-metal complex, but the present invention is notlimited thereto.

On the electron transport layer, an electron injection layer is layered.The electron injection layer may be manufactured by using a metalcomplex compound (such as Balq, Alq3, Be(bq)2, Zn(BTZ)2, Zn(phq)2, PBD,spiro-PBD, TPBI, and Tf-6P) or a low molecular material including anaromatic compound having an imidazole ring or a boron compound. Herein,the electron injection layer may be formed in a thickness range of 100 Åto 300 Å.

On the electron injection layer, a cathode is positioned. Such a cathodeperforms a role of injecting electrons into the electron injectionlayer. As a material for the cathode, the same material as that used foran anode may be used. In order to achieve efficient electron injection,a metal having a low work function is more preferable. Especially,metals such as tin, magnesium, indium, calcium, sodium, lithium,aluminum, silver, or alloys thereof may be used. Further, adouble-layered electrode (e.g., lithiumfluoride and aluminum, lithiumoxide and aluminum, and strontium oxide and aluminum) with a thicknessof 100 μm or less may be used.

The OLED according to the present invention may be manufactured in afront luminescent type, a rear luminescent type, or a both-sideluminescent type according to its materials.

Meanwhile, the present invention provides a terminal which includes adisplay device and a control part for driving the display device, thedisplay device including the above described organic electronic device.The terminal means a wired/wireless communication terminal which iscurrently used or will be used in the future. The above describedterminal according to the present invention may be a mobilecommunication terminal such as a cellular phone, and may include allkinds of terminals such as a PDA, an electronic dictionary, a PMP, aremote control, a navigation unit, a game player, various kinds of TVs,and various kinds of computers.

Example

Hereinafter, the present invention will be described more specificallywith reference to Preparation Examples and Experimental Examples.However, the following examples are only for illustrative purposes andare not intended to limit the scope of the invention.

Preparation Example

Hereinafter, Preparation Examples or Synthesis Examples of the compoundsincluding a 5-membered heterocycle, represented by Formula 1, will bedescribed. However, since there are many compounds including a5-membered heterocycle, represented by Formula 1, one compound or twocompounds from among the compounds will be exemplified. The personskilled in the art of the invention should realize that other compoundsincluding a 5-membered heterocycle can be prepared through PreparationExamples as described below although they are not exemplified.

Synthesis Method

Hereinafter, Preparation Examples or Synthesis Examples of the compoundsincluding a 5-membered heterocycle, represented by Formula 1, will bedescribed. However, since there are many compounds including a5-membered heterocycle, represented by Formula 1, one compound or twocompounds from among the compounds will be exemplified. A person skilledin the art of the invention should realize that other compoundsincluding a 5-membered heterocycle can be prepared through PreparationExamples as described below although they are not exemplified.

Synthesis Example 1

Synthesis Method of Intermediate A

Dibenzothiophene was dissolved in tetrahydrofuran, and the temperatureof the reaction product was lowered to −78° C. n-BuLi (2.5 M in hexane)was slowly added thereto, and the mixture was stirred for 1 hour at 0°C. Then, the temperature of the product was lowered to −78, and atriisopropyl borate solution dissolved in tetrahydrofuran was droppedthereto, followed by stirring for 12 hours at room temperature. Afterthe completion of the reaction, the resultant product was added with1N-HCl aqueous solution, stirred for 30 minutes, and extracted withether. From the extract, a small amount of water was removed bymagnesium sulfate anhydrous, followed by vacuum-filtration. Then, theproduct obtained after concentration of an organic solvent was purifiedby column chromatography to give a required intermediate A (yield: 71%).

Synthesis Method of Intermediate B

The intermediate A obtained from the previous step, 2-bromonitrobenzene,Pd(PPh3)4, and potassium carbonate (K₂CO₃) were dissolved intetrahydrofuran and a small amount of water, followed by reflux for 24hours. After the completion of the reaction, the reaction product wascooled to room temperature, extracted with dichloromethane (CH₂Cl₂), andwashed with water. From the extract, a small amount of water was removedby magnesium sulfate anhydrous, followed by vacuum-filtration. Then, theproduct obtained after concentration of an organic solvent was purifiedby column chromatography to give a required intermediate B (yield: 87%).

Synthesis Method of Intermediate C

The intermediate B obtained from the previous step, andtriphenylphosphine were dissolved in o-DCB(o-dichlorobenzene), followedby reflux for 24 hours. After the completion of the reaction, vacuumdistillation was carried out for removal of a solvent. Then, theconcentrated product was purified by column chromatography to give arequired intermediate C (yield: 61%).

Synthesis Method of Compound 1-3

The intermediate C obtained from the previous step, 4-bromobiphenyl,Pd2(dba)3, P(tBu)3, and NaOtBu were dissolved in a toluene solvent,followed by reflux for 6 hours at 110° C. After the completion of thereaction, the reaction product was subjected to vacuum filtrationthrough celite and silica gel by using a hot toluene solvent. Thetemperature was cooled to room temperature, and the deposited productwas recrystallized again by toluene and acetone so as to give a requiredcompound 1-3 (yield: 70%).

2. Synthesis of Compounds 2-1 and 3-1 Represented by Formulas 9 and 10Synthesis Example 2

Synthesis Method of Intermediate D

Dibenzothiophene was dissolved in carbondisulfide (CS₂), and bromine wasslowly dropped thereto. The resultant mixture was stirred at roomtemperature for 12 hours. After the completion of the reaction, theproduct produced by concentration of an organic solvent through adecompressor was recrystallized by an ethanol solvent so as to give arequired intermediate D (yield: 86%).

Synthesis Method of Intermediate E

The intermediate D obtained from the previous step was dissolved inanhydrous tetrahydrofuran, and the temperature of the reaction productwas lowered to −78° C. n-BuLi (2.5 M in hexane) was slowly droppedthereto, and the reaction temperature was stirred at 0° C. for 1 hour.Then, the temperature of the reaction product was lowered to −78° C.,and a triisopropyl borate solution dissolved in tetrahydrofuran wasdropped thereto, followed by stirring for 12 hours at room temperature.After the completion of the reaction, the resultant product was addedwith 1N-HCl aqueous solution, stirred for 30 minutes, and extracted withether. From the extract, a small amount of water was removed bymagnesium sulfate anhydrous, followed by vacuum-filtration. Then, theproduct obtained after concentration of an organic solvent was purifiedby column chromatography to give a required intermediate E (yield: 82%).

Synthesis Method of Intermediate F

The intermediate E obtained from the previous step, 2-bromonitrobenzene,Pd(PPh3)4, and potassium carbonate (K₂CO₃) were dissolved intetrahydrofuran and a small amount of water, followed by reflux for 24hours. After the completion of the reaction, the reaction product wascooled to room temperature, extracted with dichloromethane (CH₂Cl₂), andwashed with water. From the extract, a small amount of water was removedby magnesium sulfate anhydrous, followed by vacuum-filtration. Then, theproduct obtained after concentration of an organic solvent was purifiedby column chromatography to give a required intermediate F (yield: 87%).

Synthesis Method of Intermediates G and H

The intermediate F obtained from the previous step, andtriphenylphosphine were dissolved in o-DCB, followed by reflux for 24hours. After the completion of the reaction, vacuum distillation wascarried out for removal of a solvent. Then, the concentrated product waspurified by column chromatography to give required intermediates G and H(yield: 61%, ratio of G to H=6:4).

Synthesis Method of Compound 2-1

The intermediate G obtained from the previous step, bromobenzene,Pd2(dba)3, P(tBu)3, and NaOtBu were dissolved in a toluene solvent,followed by reflux for 6 hours at 110° C. After the completion of thereaction, the reaction product was subjected to vacuum filtrationthrough celite and silica gel by using a hot toluene solvent. Thetemperature was cooled to room temperature, and the deposited productwas recrystallized again by toluene and acetone so as to give a requiredcompound 2-1 (yield: 68%).

Synthesis Method of Compound 3-1

The intermediate H obtained from the previous step, bromobenzene,Pd2(dba)3, P(tBu)3, and NaOtBu were dissolved in a toluene solvent,followed by reflux for 6 hours at 110° C. After the completion of thereaction, the reaction product was subjected to vacuum filtrationthrough celite and silica gel by using a hot toluene solvent. Thetemperature was cooled to room temperature, and the deposited productwas recrystallized again by toluene and acetone so as to give a requiredcompound 3-1 (yield: 62%).

3. Synthesis of Compounds 4-3 and 5-3 Represented by Formulas 11 and 12Synthesis Example 3

Synthesis Method of Intermediate J

2-Bromocarbazole, bis(pinacolato)diboron, palladium chloride (PdCl₂)(dppf), and KOAc were dissolved in dimethylformamide, followed bystirring at 130° C. for 3 hours. After the completion of the reaction,the reaction product was cooled to room temperature, and then added withether and distilled water, followed by stirring at room temperature. Anorganic was separated from a water layer, and the separation wasrepeatedly carried out twice by the same method. The resultant productproduced through the concentration of the organic layer wasrecrystallized by acetonitrile so as to give a required intermediate J(yield: 38%).

Synthesis Method of Intermediate K

The intermediate J obtained from the previous step,1-bromo-2-(methylsulfinyl)benzene, Pd(PPh3)4, and potassium carbonatewere dissolved in tetrahydrofuran and a small amount of water, followedby reflux for 24 hours. After the completion of the reaction, thereaction product was cooled to room temperature, extracted withdichloromethane (CH₂Cl₂), and washed with water. From the extract, asmall amount of water was removed by magnesium sulfate anhydrous,followed by vacuum-filtration. Then, the product obtained afterconcentration of an organic solvent was purified by columnchromatography to give a required intermediate K (yield: 51%).

Synthesis Method of Intermediates L and 1

The intermediate K obtained from the previous step was dissolved intrifluoromethanesulfonic acid solvent, followed by stirring at roomtemperature for 48 hours. After the completion of the reaction, thereaction product was added with a mixed solvent of water and pyridine,followed by reflux for 20 minutes. The reaction product was cooled toroom temperature, extracted with dichloromethane (CH₂Cl₂), and washedwith water. From the extract, a small amount of water was removed bymagnesium sulfate anhydrous, followed by vacuum-filtration. Then, theproduct obtained after concentration of an organic solvent was purifiedby column chromatography to give required intermediates L and M (yield:38%, ratio of L to M=8:2).

Synthesis Method of Compound 4-3

The intermediate L obtained from the previous step, 4-bromobiphenyl,Pd2(dba)3, P(tBu)3, and NaOtBu were dissolved in a toluene solvent,followed by reflux for 6 hours at 110° C. After, the completion of thereaction, the reaction product was subjected to vacuum filtrationthrough celite and silica gel by using a hot toluene solvent. Thetemperature was cooled to room temperature, and the deposited productwas recrystallized again by toluene and acetone so as to give a requiredcompound 4-3 (yield: 77%).

Synthesis Method of Compound 5-3

The intermediate M obtained from the previous step, 4-bromobiphenyl,Pd2(dba)3, P(tBu)3, and NaOtBu were dissolved in a toluene solvent,followed by reflux for 6 hours at 110° C. After, the completion of thereaction, the reaction product was subjected to vacuum filtrationthrough celite and silica gel by using a hot toluene solvent. Thetemperature was cooled to room temperature, and the deposited productwas recrystallized again by toluene and acetone so as to give a requiredcompound 5-3 (yield: 63%).

4. Synthesis of Compound 6-1 Represented by Formula 13 Synthesis Example4

Synthesis Method of Intermediate N

1-Bromocarbazole, bis(pinacolato)diboron, palladium chloride(PdCl₂)(dppf), and KOAc were dissolved in dimethylformamide, followed bystirring at 130° C. for 3 hours. After the completion of the reaction,the reaction product was cooled to room temperature, and then added withether and distilled water, followed by stirring at room temperature. Anorganic was separated from a water layer, and the separation wasrepeatedly carried out twice by the same method. The resultant productproduced through the concentration of the organic layer wasrecrystallized by acetonitrile so as to give a required intermediate N(yield: 35%).

Synthesis Method of Intermediate O

The intermediate N obtained from the previous step,1-bromo-2-(methylsulfinyl)benzene, Pd(PPh3)4, and potassium carbonatewere dissolved in tetrahydrofuran and a small amount of water, followedby reflux for 24 hours. After the completion of the reaction, thereaction product was cooled to room temperature, extracted withdichloromethane (CH₂Cl₂), and washed with water. From the extract, asmall amount of water was removed by magnesium sulfate anhydrous,followed by vacuum-filtration. Then, the product obtained afterconcentration of an organic solvent was purified by columnchromatography to give a required intermediate O (yield: 62%).

Synthesis Method of Intermediate P

The intermediate O obtained from the previous step was dissolved intrifluoromethanesulfonic acid solvent, followed by stirring at roomtemperature for 48 hours. After the completion of the reaction, thereaction product was added with a mixed solvent of water and pyridine,followed by reflux for 20 minutes. The reaction product was cooled toroom temperature, extracted with dichloromethane (CH₂Cl₂), and washedwith water. From the extract, a small amount of water was removed bymagnesium sulfate anhydrous, followed by vacuum-filtration. Then, theproduct obtained after concentration of an organic solvent was purifiedby column chromatography to give a required intermediates P (yield:42%).

Synthesis Method of Compound 6-1

The intermediate P obtained from the previous step, bromobenzene,Pd2(dba)3, P(tBu)3, and NaOtBu were dissolved in a toluene solvent,followed by reflux for 6 hours at 110° C. After, the completion of thereaction, the reaction product was subjected to vacuum filtrationthrough celite and silica gel by using a hot toluene solvent. Thetemperature was cooled to room temperature, and the deposited productwas recrystallized again by toluene and acetone so as to give a requiredcompound 6-1 (yield: 75%).

Fabrication Test of Organic EL Device

An OLED was manufactured according to a conventional method by usingeach of compounds 1-3, 2-1, 3-1, 4-3, 5-3, and 6-1 obtained by synthesisas a light emitting host material for a light emitting layer. First, ona glass substrate, an ITO layer (anode) was formed with a thickness of10 nm. On the ITO layer (anode), a copper phthalocyanine (hereinafter,referred to as CuPc) film as a hole injection layer wasvacuum-deposited. Then, on this film,4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred toas a-NPD) as a hole transport compound was vacuum-deposited with athickness of 30 nm so as to form a hole transport layer. After the holetransport layer was formed, each of the compounds 1-3, 2-1, 3-1, 4-3,5-3, and 6-1 as a phosphorescence host material was deposited on thehole transport layer so as to form a light emitting layer. At the sametime, as a phosphorescent Ir metal complex dopant,tris(2-phenylpyridine)iridium (hereinafter, referred to as Ir(ppy)₃) wasadded. Herein, in the light emitting layer, the concentration ofIr(ppy)₃ was 5 wt %. As a hole blocking layer,(1,1-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, referred to as BAlq) was vacuum-deposited with a thicknessof 10 nm, and then as an electron injection layer,tris(8-quinolinol)aluminum (hereinafter, referred to as Alq₃) wasfilm-formed with a thickness of 40 nm. Then, LiF (alkali-metal halide)was deposited with a thickness of 0.2 nm, and Al was deposited with athickness of 150 nm. The Al/LiF was used as a cathode while the OLED wasfabricated.

Comparison Example

For comparison, instead of the inventive compound, a compound(hereinafter, referred to as CBP) represented by Formula below was usedas a light emitting host material so as to fabricate an OLED with thesame structure as that of Test Example.

TABLE 1 Host material current luminous chromaticity of light Voltagedensity luminance efficiency coordinates emitting layer (V) (mA/cm²)(cd/m²) (cd/A) (x, y) Example 1 compound 1-3 5.5 0.35 106 51.3 (0.30,0.60) Example 2 compound 2-1 5.8 0.33 107 47.3 (0.30, 0.60) Example 3compound 3-1 5.9 0.31 105 45.2 (0.32, 0.61) Example 4 compound 4-3 5.90.31 105 44.2 (0.30, 0.60) Example 5 compound 5-3 5.6 0.32 107 48.3(0.31, 0.61) Example 6 compound 6-1 6.1 0.31 103 43.9 (0.30, 0.60)Comparative CBP 6.1 0.31 101 32.6 (0.33, 0.61) Example 1

From the results noted in Table 1, it can be seen that in an OLED usingthe inventive material for the OLED, it is possible to obtain long-lifegreen light with a high efficiency, and an improved color purity. Thus,the inventive material as a green phosphorescence host material for anOLED can significantly improve the luminous efficiency and lifetime.

It is natural that even though the inventive compounds are applied toother organic material layers of an OLED, e.g., a light emitting layer,an auxiliary light emitting layer, an electron injection layer, anelectron transport layer, and a hole injection layer as well as a holetransport layer, it is possible to achieve the same effects.

Although a preferred embodiment of the present invention has beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentsdisclosed in the present invention are intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment.

The scope of the present invention shall be construed on the basis ofthe accompanying claims in such a manner that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

1: A compound represented by Formula below, or a derivative compoundthereof:

in Formula above, R₁, R₃ through R₈, and R₁₀ each are independentlyselected from the group consisting of a hydrogen atom, a halogen atom, acyano group, an alkoxy group, a thiol group, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted alkoxy group having 1′ to 50 carbon atoms, a substitutedor unsubstituted alkenyl group having 2 to 50 carbon atoms, asubstituted or unsubstituted arylene group having 6 to 60 carbon atoms,a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, asubstituted or unsubstituted aryloxy group having 6 to 60 carbon atoms,a substituted or unsubstituted C₁-C₅₀ alkyl group having at least one ofsulfur (S), nitrogen (N), oxygen (O), phosphorous (P) and silicon (Si),a substituted or unsubstituted C₅-C₆₀ heteroaryl group having at leastone heteroatom selected from the group consisting of sulfur (S),nitrogen (N), oxygen (O), phosphorous (P) and silicon (Si), and asubstituted or unsubstituted C₅-C₆₀ heteroaryloxy group having at leastone of sulfur, nitrogen, oxygen, phosphorous and silicon; R₂ and R₉ arehydrogen; X is at least one selected from sulfur, oxygen or silicon, Yis selected from the group consisting of a hydrogen atom, a halogenatom, a cyano group, an alkoxy group, a thiol group, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted alkenyl group having 2 to 50 carbon atoms, a substitutedor unsubstituted arylene group having 6 to 60 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 60 carbon atoms, asubstituted or unsubstituted aryloxy group having 6 to 60 carbon atoms,a substituted or unsubstituted C₁-C₅₀ alkyl group having at least one ofsulfur, nitrogen, oxygen, phosphorous and silicon, a substituted orunsubstituted C₅-C₆₀ heteroaryl group having at least one heteroatomselected from the group consisting of sulfur, nitrogen, oxygen,phosphorous and silicon, and a substituted or unsubstituted C₅-C₆₀heteroaryloxy group having at least one of sulfur, nitrogen, oxygen,phosphorous and silicon, and n is an integer from 1 to 3, wherein thecompound is a compound other than a compound represented by the aboveFormula wherein each of R1 through R10 is a hydrogen atom, A is an arylhaving 6 carbon atoms, a ring comprising X is thiophene, Y is asubstituted or unsubstituted C5-C60 heteroaryl group having nitrogen;and n is
 1. 2: The compound as claimed in claim 1, wherein R₁ throughR₁₀ each optionally form a substituted or unsubstituted saturated orunsaturated ring together with an adjacent group. 3: The compound asclaimed in claim 1, wherein the compound is any one of compounds below:

4: The compound as claimed in claim 2, wherein the compound is any oneof compounds below:

5: An organic electronic device comprising one or more organic materiallayers comprising the compound as claimed in claim
 1. 6: The organicelectronic device as claimed in claim 5, wherein the organic materiallayers are formed by a soluble process of the compound. 7: The organicelectronic device as claimed in claim 5, wherein the organic electronicdevice is an organic light emitting diode in which a first electrode,said one or more organic material layers, and a second electrode aresequentially layered. 8: The organic electronic device as claimed inclaim 7, wherein the organic material layers comprise any one of a holeinjection layer, a hole transport layer, a light emitting layer, anelectron transport layer, and an electron injection layer. 9: Theorganic electronic device as claimed in claim 7, wherein the organicmaterial layers comprise a light emitting layer, and in the lightemitting layer, the compound is used as a host or dopant material. 10: Aterminal comprising a display device and a control part for driving thedisplay device, the display device comprising the organic electronicdevice as claimed in claim
 7. 11: The terminal as claimed in claim 10,wherein the organic electronic device is any one of an organic lightemitting diode (OLED), an organic solar cell, an organic photo conductor(OPC) drum, and an organic transistor (organic TFT). 12: The compound asclaimed in claim 1, wherein Y is a substituted or unsubstituted arylgroup having 6 to 60 carbon atoms. 13: The compound as claimed in claim1, wherein Y is a substituted or unsubstituted C₅-C₆₀ heteroaryl grouphaving at least one of sulfur, nitrogen, oxygen, phosphorous andsilicon. 14: The compound as claimed in claim 1, wherein R₁, R₃ throughR₈, and R₁₀ each are hydrogen. 15: The compound as claimed in claim 1,wherein the compound is any one of compounds below:

16: The compound as claimed in claim 1, wherein the compound is any oneof compounds below:

17: The compound as claimed in claim 1, wherein the compound is any oneof compounds below: